# Electronic Supplementary Material (ESI) for Nanoscale.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1870227'
_audit_update_record             
;
2018-09-27 deposited with the CCDC.
2019-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C72 H6 Cl6'
_chemical_formula_weight         1083.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8783(11)
_cell_length_b                   9.9409(11)
_cell_length_c                   12.3344(14)
_cell_angle_alpha                70.99(2)
_cell_angle_beta                 75.17(2)
_cell_angle_gamma                63.05(2)
_cell_volume                     1012.3(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2892
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      28.65

_exptl_crystal_description       block
_exptl_crystal_colour            dark-purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_F_000             540
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.484
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6136
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10599
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.761
_diffrn_reflns_theta_max         28.719
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5188
_reflns_number_gt                3781
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+0.7066P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5188
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1068
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.42897(6) 0.95831(7) 0.19114(5) 0.03081(14) Uani 1 1 d . . . . .
Cl2 Cl 0.11863(6) 1.13311(7) 0.08141(5) 0.03582(15) Uani 1 1 d . . . . .
Cl3 Cl 0.31388(7) 0.70262(8) -0.15943(5) 0.04063(16) Uani 1 1 d . . . . .
C1 C 0.3973(2) 0.8895(2) 0.09224(17) 0.0221(4) Uani 1 1 d . . . . .
C2 C 0.2609(2) 0.9668(2) 0.04403(17) 0.0220(4) Uani 1 1 d . . . . .
C3 C 0.2347(2) 0.9089(2) -0.03315(17) 0.0237(4) Uani 1 1 d . . . . .
H3 H 0.1410 0.9605 -0.0653 0.028 Uiso 1 1 calc R U . . .
C4 C 0.3476(2) 0.7746(2) -0.06261(18) 0.0254(4) Uani 1 1 d . . . . .
C5 C 0.4849(2) 0.6967(3) -0.01621(19) 0.0273(5) Uani 1 1 d . . . . .
H5 H 0.5614 0.6048 -0.0375 0.033 Uiso 1 1 calc R U . . .
C6 C 0.5084(2) 0.7550(2) 0.06158(18) 0.0265(4) Uani 1 1 d . . . . .
H6 H 0.6017 0.7024 0.0944 0.032 Uiso 1 1 calc R U . . .
C7 C 0.0983(3) 1.1210(3) -0.3169(2) 0.0366(6) Uani 1 1 d . . . . .
C8 C 0.2267(3) 1.1552(3) -0.3152(2) 0.0362(6) Uani 1 1 d . . . . .
C9 C 0.1729(3) 1.2681(3) -0.24609(19) 0.0346(5) Uani 1 1 d . . . . .
C10 C 0.0109(3) 1.3016(3) -0.20467(19) 0.0379(6) Uani 1 1 d . . . . .
C11 C 0.2248(3) 1.3852(3) -0.2782(2) 0.0350(5) Uani 1 1 d . . . . .
C12 C 0.1190(3) 1.5423(3) -0.2703(2) 0.0373(6) Uani 1 1 d . . . . .
C13 C 0.1640(3) 1.6489(3) -0.3689(3) 0.0430(7) Uani 1 1 d . . . . .
C14 C 0.2979(2) 1.5569(3) -0.4387(2) 0.0355(6) Uani 1 1 d . . . . .
C15 C 0.3344(2) 1.3932(3) -0.3808(2) 0.0307(5) Uani 1 1 d . . . . .
C16 C 0.3861(2) 1.2853(3) -0.4461(2) 0.0288(5) Uani 1 1 d . . . . .
C17 C 0.3304(2) 1.1634(3) -0.4129(2) 0.0347(5) Uani 1 1 d . . . . .
C18 C 0.3111(3) 1.1391(3) -0.5184(2) 0.0364(6) Uani 1 1 d . . . . .
C19 C 0.1892(3) 1.1081(3) -0.5198(2) 0.0384(6) Uani 1 1 d . . . . .
C20 C 0.1070(3) 1.1820(3) -0.6197(2) 0.0385(6) Uani 1 1 d . . . . .
C21 C 0.1517(3) 1.2846(3) -0.7130(2) 0.0405(6) Uani 1 1 d . . . . .
C22 C 0.0342(3) 1.4272(3) -0.7702(2) 0.0416(6) Uani 1 1 d . . . . .
C23 C 0.0895(3) 1.5484(4) -0.8027(2) 0.0428(7) Uani 1 1 d . . . . .
C24 C 0.2410(3) 1.4806(3) -0.7665(2) 0.0416(6) Uani 1 1 d . . . . .
C25 C 0.2784(3) 1.3159(3) -0.7101(2) 0.0385(6) Uani 1 1 d . . . . .
C26 C 0.3566(2) 1.2446(3) -0.6152(2) 0.0362(6) Uani 1 1 d . . . . .
C27 C 0.4030(2) 1.3357(3) -0.5709(2) 0.0338(5) Uani 1 1 d . . . . .
C28 C 0.3679(2) 1.4905(3) -0.6245(2) 0.0365(6) Uani 1 1 d . . . . .
C29 C 0.2839(3) 1.5644(3) -0.7256(2) 0.0407(6) Uani 1 1 d . . . . .
C30 C 0.1787(3) 1.7233(3) -0.7171(2) 0.0379(6) Uani 1 1 d . . . . .
C31 C 0.1981(3) 1.7462(3) -0.6147(2) 0.0382(6) Uani 1 1 d . . . . .
C32 C 0.3154(3) 1.6016(3) -0.5573(2) 0.0366(6) Uani 1 1 d . . . . .
C33 C 0.0542(3) 1.7825(3) -0.4227(3) 0.0443(7) Uani 1 1 d . . . . .
C34 C 0.0721(3) 1.8334(3) -0.5491(2) 0.0375(6) Uani 1 1 d . . . . .
C35 C -0.0802(3) 1.9019(3) -0.5838(2) 0.0383(6) Uani 1 1 d . . . . .
C36 C 0.0331(3) 1.7891(3) -0.7509(2) 0.0368(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.728(2) . ?
Cl2 C2 1.726(2) . ?
Cl3 C4 1.739(2) . ?
C1 C6 1.386(3) . ?
C1 C2 1.391(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.385(3) . ?
C4 C5 1.387(3) . ?
C5 C6 1.382(3) . ?
C7 C35 1.383(4) 2_584 ?
C7 C36 1.436(4) 2_584 ?
C7 C8 1.461(3) . ?
C8 C17 1.374(4) . ?
C8 C9 1.456(4) . ?
C9 C11 1.382(4) . ?
C9 C10 1.463(3) . ?
C10 C23 1.385(4) 2_584 ?
C10 C36 1.450(4) 2_584 ?
C11 C15 1.446(3) . ?
C11 C12 1.452(3) . ?
C12 C22 1.388(4) 2_584 ?
C12 C13 1.452(4) . ?
C13 C33 1.367(4) . ?
C13 C14 1.470(4) . ?
C14 C32 1.373(4) . ?
C14 C15 1.460(3) . ?
C15 C16 1.384(3) . ?
C16 C27 1.445(3) . ?
C16 C17 1.451(3) . ?
C17 C18 1.470(4) . ?
C18 C19 1.377(4) . ?
C18 C26 1.437(4) . ?
C19 C20 1.449(4) . ?
C19 C35 1.453(4) 2_584 ?
C20 C21 1.393(4) . ?
C20 C33 1.456(4) 2_584 ?
C21 C25 1.431(4) . ?
C21 C22 1.460(4) . ?
C22 C12 1.388(4) 2_584 ?
C22 C23 1.443(4) . ?
C23 C10 1.385(4) 2_584 ?
C23 C24 1.458(4) . ?
C24 C29 1.353(4) . ?
C24 C25 1.464(4) . ?
C25 C26 1.377(4) . ?
C26 C27 1.467(3) . ?
C27 C28 1.377(4) . ?
C28 C32 1.426(4) . ?
C28 C29 1.470(4) . ?
C29 C30 1.466(4) . ?
C30 C36 1.395(3) . ?
C30 C31 1.427(4) . ?
C31 C34 1.385(4) . ?
C31 C32 1.469(3) . ?
C33 C20 1.456(4) 2_584 ?
C33 C34 1.464(4) . ?
C34 C35 1.457(4) . ?
C35 C7 1.383(4) 2_584 ?
C35 C19 1.453(4) 2_584 ?
C36 C7 1.436(4) 2_584 ?
C36 C10 1.450(4) 2_584 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.69(19) . . ?
C6 C1 Cl1 119.65(16) . . ?
C2 C1 Cl1 120.66(16) . . ?
C3 C2 C1 120.37(19) . . ?
C3 C2 Cl2 118.50(15) . . ?
C1 C2 Cl2 121.11(16) . . ?
C4 C3 C2 118.86(19) . . ?
C3 C4 C5 121.6(2) . . ?
C3 C4 Cl3 118.59(16) . . ?
C5 C4 Cl3 119.81(16) . . ?
C6 C5 C4 118.80(19) . . ?
C5 C6 C1 120.68(19) . . ?
C35 C7 C36 119.7(2) 2_584 2_584 ?
C35 C7 C8 120.4(2) 2_584 . ?
C36 C7 C8 108.0(2) 2_584 . ?
C17 C8 C9 120.3(2) . . ?
C17 C8 C7 119.5(2) . . ?
C9 C8 C7 108.2(2) . . ?
C11 C9 C8 120.5(2) . . ?
C11 C9 C10 120.4(2) . . ?
C8 C9 C10 107.1(2) . . ?
C23 C10 C36 120.4(2) 2_584 2_584 ?
C23 C10 C9 119.2(2) 2_584 . ?
C36 C10 C9 108.2(2) 2_584 . ?
C9 C11 C15 119.1(2) . . ?
C9 C11 C12 120.2(2) . . ?
C15 C11 C12 108.8(2) . . ?
C22 C12 C11 119.1(2) 2_584 . ?
C22 C12 C13 121.2(2) 2_584 . ?
C11 C12 C13 107.6(2) . . ?
C33 C13 C12 119.8(3) . . ?
C33 C13 C14 119.6(3) . . ?
C12 C13 C14 108.4(2) . . ?
C32 C14 C15 119.4(2) . . ?
C32 C14 C13 121.5(2) . . ?
C15 C14 C13 107.1(2) . . ?
C16 C15 C11 120.4(2) . . ?
C16 C15 C14 119.6(2) . . ?
C11 C15 C14 108.2(2) . . ?
C15 C16 C27 119.8(2) . . ?
C15 C16 C17 120.4(2) . . ?
C27 C16 C17 107.7(2) . . ?
C8 C17 C16 119.3(2) . . ?
C8 C17 C18 120.1(2) . . ?
C16 C17 C18 108.4(2) . . ?
C19 C18 C26 120.4(2) . . ?
C19 C18 C17 120.2(2) . . ?
C26 C18 C17 107.4(2) . . ?
C18 C19 C20 119.6(2) . . ?
C18 C19 C35 119.7(2) . 2_584 ?
C20 C19 C35 108.8(2) . 2_584 ?
C21 C20 C19 119.6(2) . . ?
C21 C20 C33 120.8(2) . 2_584 ?
C19 C20 C33 107.2(2) . 2_584 ?
C20 C21 C25 120.1(2) . . ?
C20 C21 C22 119.1(2) . . ?
C25 C21 C22 109.2(2) . . ?
C12 C22 C23 121.0(2) 2_584 . ?
C12 C22 C21 119.2(3) 2_584 . ?
C23 C22 C21 107.5(2) . . ?
C10 C23 C22 120.1(2) 2_584 . ?
C10 C23 C24 120.2(3) 2_584 . ?
C22 C23 C24 108.0(2) . . ?
C29 C24 C23 120.0(3) . . ?
C29 C24 C25 119.9(2) . . ?
C23 C24 C25 108.0(2) . . ?
C26 C25 C21 120.1(3) . . ?
C26 C25 C24 120.8(2) . . ?
C21 C25 C24 107.3(2) . . ?
C25 C26 C18 120.2(2) . . ?
C25 C26 C27 119.2(2) . . ?
C18 C26 C27 108.3(2) . . ?
C28 C27 C16 120.1(2) . . ?
C28 C27 C26 119.8(2) . . ?
C16 C27 C26 108.2(2) . . ?
C27 C28 C32 120.2(2) . . ?
C27 C28 C29 120.1(2) . . ?
C32 C28 C29 107.8(2) . . ?
C24 C29 C30 120.4(2) . . ?
C24 C29 C28 120.2(2) . . ?
C30 C29 C28 107.4(2) . . ?
C36 C30 C31 119.9(2) . . ?
C36 C30 C29 120.2(2) . . ?
C31 C30 C29 108.1(2) . . ?
C34 C31 C30 119.8(2) . . ?
C34 C31 C32 119.9(2) . . ?
C30 C31 C32 108.2(2) . . ?
C14 C32 C28 120.9(2) . . ?
C14 C32 C31 118.7(2) . . ?
C28 C32 C31 108.5(2) . . ?
C13 C33 C20 119.9(3) . 2_584 ?
C13 C33 C34 119.7(3) . . ?
C20 C33 C34 108.8(2) 2_584 . ?
C31 C34 C35 120.5(2) . . ?
C31 C34 C33 120.6(2) . . ?
C35 C34 C33 106.9(2) . . ?
C7 C35 C19 120.1(2) 2_584 2_584 ?
C7 C35 C34 119.4(2) 2_584 . ?
C19 C35 C34 108.2(2) 2_584 . ?
C30 C36 C7 120.7(2) . 2_584 ?
C30 C36 C10 118.9(2) . 2_584 ?
C7 C36 C10 108.5(2) 2_584 2_584 ?

_refine_diff_density_max         0.652
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.063

